Our tax laws create categories–income/exclusion, deduction, and credit. Taxpayers are presented with structured forms that set out these categories. The IRS expects taxpayers to fill out the forms by correctly identifying what items go in each category. But it is not always clear what items go in each category. Taxpayers may engage in tax planning…
Category: Federal Income Tax
Federal Income Tax
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How to Substantiate Gambling Tax Losses
There are several types of tax disputes that are frequently litigated. Gambling losses are an example. Taxpayers who gamble often incur significant losses. If the taxpayer is found to be a professional gambler, these losses can be counted for income tax purposes and used to offset the taxpayer’s other income. These tax losses can reduce…
IRS Expands Sec. 9100 Relief for Late Forms 3115
As innocuous as it sounds, the Form 3115 is a tax form like no other. A Form 3115 that is inadvertently omitted from a tax return filing can result in sizable differences in tax and trigger significant tax penalties and interest. Given the amounts that are often reported on the Form 3115, errors could cost…
Converting Home to Rental to Get Tax Loss Deduction
If you move out of a house and rent it to a friend for less than fair market value rent, can you then take a tax loss on the subsequent sale of the house? If the home is not converted to a rental property, the loss is disallowed as a personal tax loss. If the…
Meal & Entertainment: The IRS Auditors “Bread & Butter”
I once worked with an IRS agent who would only make two types of adjustments. He would make UNICAP/inventory adjustments and meal and entertainment adjustments. If either of these items could be adjusted for a tax return, he would adjust them. It didn’t matter what else was listed on the tax return. It did not…
Tax on Virtual Currency Received for Microtasks
Our Federal income tax laws take a broad view of what counts as income and gain. The tax law then imposes a ridged framework for classifying and computing tax on income or gain. By casting the net wide, the tax law is able to capture just about every type of transaction that one could dream…
What is a Rental Activity?
The ability to generate current year tax losses is a strong incentive for high-income taxpayers to own real estate. Real estate often produces tax losses, but not economic losses. This happens because the current operating expenses plus tax depreciation result in a current year loss. At the same time, the property likely increased in value…
Divorce Payments & Tax Basis in Business
Our Federal income tax laws often build upon the presumption that seemingly adverse parties are actually adverse. Our tax laws do not always account for instances where the parties are actively working in concert to reduce the IRS’s cut. Transfers and payments made in relation to divorce are an example. With our tax laws, it…
When is Rental Real Estate a Business?
Our tax laws are not perfect. There are grey areas. Most of these grey areas are of little consequence as they do not have a significant impact on the amount of tax that is due. There are other grey areas that can significantly impact the amount of tax due. These tax disputes are frequently litigated.…
Avoiding Tax on Discharge of a Mortgage
There are times in life when you may feel that you can’t get ahead. One step forward, two steps back–as they say. Paying income tax on debt that you avoid is an example. You negotiate with the lender or creditor and they agree to settle the balance for less. One step forward. Then a few…